Hello Steve,

This question may sound like I’m biting off more than I can chew, however my wife and I are fully committed to doing it anyway. The house is on the market and we’ve promised ourselves that we’ll give it at least one year before we make our minds up whether to keep sailing or return to landlubbers.

I am 41 year old, have almost no sailing experience other than going out on our local bay (Morton bay–Brisbane Australia) with friends on their mid 20ft day-sailers. This is where we (my wife and I ) intend to live aboard and learn to sail until I feel confident enough to coastal sail the 400 miles up to the Whitsunday Island group, and then offshore to the South Pacific Islands and beyond when we’re ready!

Just so you understand my reasoning in learning to sail this way, as opposed to getting a small kneel boat first, I wish to live aboard now, I have always found it easier and quicker for ME to learn by jumping in with both feet. I don’t learn easily in a structured environment, ie: sailing school, I enjoy a challenge. I quite often have people say to me after they get to know me "is there anything that you can’t do!" Some examples–I’ve built my own house from start to finish using no other trades except electrician, it is being sold as I write this for over half a million dollars (this is our cruising kitty) or rebuilding the Isuzu turbo diesel in my 4×4 campervan in remote central Australia when it split the skirting on a piston, I’d never worked on a diesel before.

I have just retired from 17 years as a professional motorcycle racer. This has taught me to trust my own judgment, recognise the difference between fear and danger, anticipate consequences and problems before they happen and never to let anxiety or fear cloud your judgment. As strange as it seems I think these qualities should be a good base from which to jump into the world of cruising. Oh and I grew up on a remote outback cattle station, so being isolated and self reliant is second nature to me.

Ok, now you’re probably thinking this guys got a couple of kangaroo’s loose in the top paddock.

Here’s what I am thinking:
Spending a total of about $150,000 AUS (this will leave us with 2 rental houses debt free for income )
A steel, aluminum or cold moulded wood boat (no doubt I’ll run aground while I’m learning) with a good size engine to pull us off a lee shore while learning too.
34-38 ft ( although my 24 year old cousin who has been the youngest captain ever to do the Sydney to Hobart races including the 1998 storm when he was just 19, says get a 40+ ft boat as it won’t be any harder to learn to sail than the smaller boat and be much better to live aboard)

After reading your sensational OFFSHORE CRUISING ENCYCLOPEDIA, on page 1123 HIO AVAE a Santana 37, I would be very interested on what you would think of this for our first boat?

I guess my biggest question is, should I buy a smaller coastal cruiser and then in a couple of years buy a bigger offshore blue water boat or put up with the inconveniences of a bigger blue water boat while we learn coastal cruising ( I am assuming that it would take at least a year to learn to sail any new boat to its full potential, so selling a coastal cruiser in couple of years then learning a new bigger blue water boat may be counter productive?

Should it be a more traditional design with heavy displacement, full keel etc. which will cope more easily with my mistakes while I’m learning or a boat with a fin keel canoe shaped hull that you favour?

I will probably have my cousin help in choosing from a short list of half-dozen boats the final boat, as he will have a better understanding of a good layout for systems on deck and living under deck.

Regards Peter